2,5-dioxopyrrolidin-1-yl 6-(2-iodoacetamido)hexanoate

• ChemBase ID: 131019
• Molecular Formular: C12H17IN2O5
• Molecular Mass: 396.17825
• Monoisotopic Mass: 396.01821965
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CI
• Canonical SMILES: ICC(=O)NCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C12H17IN2O5/c13-8-9(16)14-7-3-1-2-4-12(19)20-15-10(17)5-6-11(15)18/h1-8H2,(H,14,16)
• InChIKey: GRNALJOZUYFKSS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-(2-iodoacetamido)hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-(2-iodoacetamido)hexanoate
• Synonyms: 6-(Iodoacetamido)hexanoic acid N-hydroxysuccinimide ester

Database IDs

• CAS Number: 134759-23-2
• MDL Number: MFCD00132999
• PubChem SID: 162225297
• PubChem CID: 4378573

CALCULATED PROPERTIES

• Polarizability: 30.758177 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• Acid pKa: 12.844985
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.40132856
• LogD (pH = 7.4): 0.4013272
• Log P: 0.40132856
• Molar Refractivity: 77.7412 cm^3

PROPERTIES

Physical Property

• Solubility: DMF: soluble; methanol: soluble50 mg/mL

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - I1007

Application
A heterobifunctional cross-linking reagent containing an extended spacer with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5) Second coupling specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 7.5 (7.0-8.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Provides a 9-atom linker.
Caution
The iodoacetyl group is light sensitive.